Chemometric Approach in Studying of the Retention Behavior and Lipophilicity of Potentially Biologically Active N-Substituted-2-phenylacetamide Derivatives
Abstract
The potential biological activity of a molecule largely depends on its lipophilicity. The lipophilicity of derivatives of N-substituted-2-phenylacetamide was investigated experimentally, by applying thin-layer chromatography on reversed phase (RP-TLC on RP 18 F-254s) in the presence of ethanol and dioxane and by using relevant software packages. In order to establish dependence between lipophilicity obtained in different ways, linear regression analysis and multivariate methods were used. Approximately similar groupings of lipophilic parameters and tested compounds were registered in case of both chemometric methods. The obtained results confirm the fact that the applied linear regression analysis and multivariate analysis provide opportunities for comparing chromatographic retention data and lipophilic parameters of the investigated phenylacetamide derivatives. Results suggest that the lipophilicity of investigated molecules largely depends on the nature of the substituents linked to ...nitrogen atom and on the other hand that the chromatographic retention constants, R-M(0), determined by RP-TLC method, are similar to the standard measure of lipophilicity, log P, which makes this method appropriate for predicting lipophilicity.
Keywords:
N-substituted-2-phenylacetamides / lipophilicity / RP-TLC / chemometricsSource:
Journal of the Brazilian Chemical Society, 2014, 25, 11, 1948-1955Publisher:
- Soc Brasileira Quimica, Sao Paulo
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.5935/0103-5053.20140174
ISSN: 0103-5053
WoS: 000345241700004
Scopus: 2-s2.0-84908680756
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Vastag, Gyongyi AU - Apostolov, Suzana AU - Matijević, Borko M. AU - Marinković, Aleksandar PY - 2014 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2717 AB - The potential biological activity of a molecule largely depends on its lipophilicity. The lipophilicity of derivatives of N-substituted-2-phenylacetamide was investigated experimentally, by applying thin-layer chromatography on reversed phase (RP-TLC on RP 18 F-254s) in the presence of ethanol and dioxane and by using relevant software packages. In order to establish dependence between lipophilicity obtained in different ways, linear regression analysis and multivariate methods were used. Approximately similar groupings of lipophilic parameters and tested compounds were registered in case of both chemometric methods. The obtained results confirm the fact that the applied linear regression analysis and multivariate analysis provide opportunities for comparing chromatographic retention data and lipophilic parameters of the investigated phenylacetamide derivatives. Results suggest that the lipophilicity of investigated molecules largely depends on the nature of the substituents linked to nitrogen atom and on the other hand that the chromatographic retention constants, R-M(0), determined by RP-TLC method, are similar to the standard measure of lipophilicity, log P, which makes this method appropriate for predicting lipophilicity. PB - Soc Brasileira Quimica, Sao Paulo T2 - Journal of the Brazilian Chemical Society T1 - Chemometric Approach in Studying of the Retention Behavior and Lipophilicity of Potentially Biologically Active N-Substituted-2-phenylacetamide Derivatives EP - 1955 IS - 11 SP - 1948 VL - 25 DO - 10.5935/0103-5053.20140174 ER -
@article{ author = "Vastag, Gyongyi and Apostolov, Suzana and Matijević, Borko M. and Marinković, Aleksandar", year = "2014", abstract = "The potential biological activity of a molecule largely depends on its lipophilicity. The lipophilicity of derivatives of N-substituted-2-phenylacetamide was investigated experimentally, by applying thin-layer chromatography on reversed phase (RP-TLC on RP 18 F-254s) in the presence of ethanol and dioxane and by using relevant software packages. In order to establish dependence between lipophilicity obtained in different ways, linear regression analysis and multivariate methods were used. Approximately similar groupings of lipophilic parameters and tested compounds were registered in case of both chemometric methods. The obtained results confirm the fact that the applied linear regression analysis and multivariate analysis provide opportunities for comparing chromatographic retention data and lipophilic parameters of the investigated phenylacetamide derivatives. Results suggest that the lipophilicity of investigated molecules largely depends on the nature of the substituents linked to nitrogen atom and on the other hand that the chromatographic retention constants, R-M(0), determined by RP-TLC method, are similar to the standard measure of lipophilicity, log P, which makes this method appropriate for predicting lipophilicity.", publisher = "Soc Brasileira Quimica, Sao Paulo", journal = "Journal of the Brazilian Chemical Society", title = "Chemometric Approach in Studying of the Retention Behavior and Lipophilicity of Potentially Biologically Active N-Substituted-2-phenylacetamide Derivatives", pages = "1955-1948", number = "11", volume = "25", doi = "10.5935/0103-5053.20140174" }
Vastag, G., Apostolov, S., Matijević, B. M.,& Marinković, A.. (2014). Chemometric Approach in Studying of the Retention Behavior and Lipophilicity of Potentially Biologically Active N-Substituted-2-phenylacetamide Derivatives. in Journal of the Brazilian Chemical Society Soc Brasileira Quimica, Sao Paulo., 25(11), 1948-1955. https://doi.org/10.5935/0103-5053.20140174
Vastag G, Apostolov S, Matijević BM, Marinković A. Chemometric Approach in Studying of the Retention Behavior and Lipophilicity of Potentially Biologically Active N-Substituted-2-phenylacetamide Derivatives. in Journal of the Brazilian Chemical Society. 2014;25(11):1948-1955. doi:10.5935/0103-5053.20140174 .
Vastag, Gyongyi, Apostolov, Suzana, Matijević, Borko M., Marinković, Aleksandar, "Chemometric Approach in Studying of the Retention Behavior and Lipophilicity of Potentially Biologically Active N-Substituted-2-phenylacetamide Derivatives" in Journal of the Brazilian Chemical Society, 25, no. 11 (2014):1948-1955, https://doi.org/10.5935/0103-5053.20140174 . .